{"title":"基于 [1,3]- 质子转移反应获得光学活性四氟乙烯胺。","authors":"Yuta Kabumoto, Eiichiro Yoshimoto, Bing Xiaohuan, Masato Morita, Motohiro Yasui, Shigeyuki Yamada, Tsutomu Konno","doi":"10.3762/bjoc.20.233","DOIUrl":null,"url":null,"abstract":"<p><p>Treatment of various (<i>R</i>)-<i>N</i>-(2,2,3,3-tetrafluoropent-4-en-1-ylidene)-1-phenylethylamine derivatives with 2.4 equiv of DBU in toluene at room temperature to 50 °C for 24 h led to a smooth [1,3]-proton shift reaction with a high chirality transfer, affording the corresponding rearranged products in acceptable yields. Without purification, these products were subjected to acid hydrolysis and the subsequent <i>N</i>-Cbz protection, providing the optically active tetrafluoroethylenated amides in moderate three-step yields.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2776-2783"},"PeriodicalIF":2.2000,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11533114/pdf/","citationCount":"0","resultStr":"{\"title\":\"Access to optically active tetrafluoroethylenated amines based on [1,3]-proton shift reaction.\",\"authors\":\"Yuta Kabumoto, Eiichiro Yoshimoto, Bing Xiaohuan, Masato Morita, Motohiro Yasui, Shigeyuki Yamada, Tsutomu Konno\",\"doi\":\"10.3762/bjoc.20.233\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>Treatment of various (<i>R</i>)-<i>N</i>-(2,2,3,3-tetrafluoropent-4-en-1-ylidene)-1-phenylethylamine derivatives with 2.4 equiv of DBU in toluene at room temperature to 50 °C for 24 h led to a smooth [1,3]-proton shift reaction with a high chirality transfer, affording the corresponding rearranged products in acceptable yields. Without purification, these products were subjected to acid hydrolysis and the subsequent <i>N</i>-Cbz protection, providing the optically active tetrafluoroethylenated amides in moderate three-step yields.</p>\",\"PeriodicalId\":8756,\"journal\":{\"name\":\"Beilstein Journal of Organic Chemistry\",\"volume\":\"20 \",\"pages\":\"2776-2783\"},\"PeriodicalIF\":2.2000,\"publicationDate\":\"2024-11-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11533114/pdf/\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Beilstein Journal of Organic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.3762/bjoc.20.233\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2024/1/1 0:00:00\",\"PubModel\":\"eCollection\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Beilstein Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.3762/bjoc.20.233","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/1/1 0:00:00","PubModel":"eCollection","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Access to optically active tetrafluoroethylenated amines based on [1,3]-proton shift reaction.
Treatment of various (R)-N-(2,2,3,3-tetrafluoropent-4-en-1-ylidene)-1-phenylethylamine derivatives with 2.4 equiv of DBU in toluene at room temperature to 50 °C for 24 h led to a smooth [1,3]-proton shift reaction with a high chirality transfer, affording the corresponding rearranged products in acceptable yields. Without purification, these products were subjected to acid hydrolysis and the subsequent N-Cbz protection, providing the optically active tetrafluoroethylenated amides in moderate three-step yields.
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The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry.
The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.
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